Identify the starting material and the target molecule. The starting compound is an alkene with the formula CH3(CH2)CH=CH2, and the target is CH3CH2CH2C≡CH, which contains a terminal alkyne.
Recognize that converting an alkene to a terminal alkyne involves two main transformations: first, halogenation of the alkene to form a vicinal dihalide, and second, double dehydrohalogenation to form the alkyne.
Step 1: Use bromine (Br\_2) in the presence of light (hv) to add bromine atoms across the double bond, producing a vicinal dibromide intermediate.
Step 2: Treat the vicinal dibromide with a strong base such as sodium amide (NaNH\_2) to perform two consecutive elimination reactions (double dehydrohalogenation), removing two equivalents of HBr and forming the terminal alkyne.
Confirm that the reagents Br\_2/hv followed by NaNH\_2 are appropriate for this transformation, as other reagent sets either do not form the dibromide intermediate or are not strong enough bases to induce double elimination.